What's your childhood best friend doing now?

My best friend from elementary school was the skinniest, mouthiest little kid (one year behind me). He drove everyone nuts. But he got a girlfriend before I did in middle school and I was tremendously jealous. I was his editor at the high school paper and he continued to drive me nuts. But we were neighbors and liked to play tennis and Atari and cribbage and his mom was a great cook.

I went into journalism and he went on to become an electrical engineer who married his equally rail-thin high-school sweetheart, who is now a school principal. And the mouthy kid is now a popular member of town council. So he should be doing quite well.

I met up with them a year ago and first off they are both HUGE. Unbelievably large.

I also know (our moms are good friends) that they have a ton of financial issues due to her constant overspending. I make just below a typical engineer’s wages (I have a lot of neighbors in that field) but my wife is a SAHM; we have four kids and they have two; and we have a nice but not opulent two-story house on a big spread in a nice neighborhood outside Philly. The engineer and the principal live in a two-story row-home in the podunk town where we grew up, worth probably a third of mine. And they have expressed constant jealousy to BF’s sister, who just built a nice house of her own, so it’s not like they’re just living a different version of the dream.

Puzzling. I think if I had that kind of money I wouldn’t know what to do with it all.

You would be shocked. My husband is a car salesman (yeah, yeah, I know … you can hold the public stoning in a minute when I’m done) and he sees little snapshots of financial situations as a result. He’s had a customer with an income of $16,000/month whose financial house was so trashed he couldn’t finance a used Malibu. And then he had a couple walk in with a combined household income of about $30,000/year that paid cash for a new SUV (can’t remember which kind). They’d saved up and saved up, and when they had enough, they bought it.

You’d think that being able to pull down a big paycheck would mean you’d have the wherewithal to not be an idiot with the money, but you’d be wrong.